Mr. Stillman's Opus

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Some people keep working because they love what they do. Others stay because retirement feels financially, socially, or emotionally uncertain. In this episode, Jake explores the different forces that ca...

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Trump Accounts may offer families a valuable new way to save, but they are not automatically the right solution for every goal. In this episode, John and Jake explain how these accounts work, where they...

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John addresses the obvious right away: it’s not just him anymore, and everyone should get used to seeing Jake because he isn’t going anywhere. In this episode, John welcomes longtime friend ...

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After 40+ years in the same home, the idea of packing up and moving somewhere new—like Florida—can feel both exciting and overwhelming. The tax savings might look great on paper, but there&r...

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You can’t go back and fix the past, but you can make smarter decisions moving forward. John tackles a question a lot of people quietly wrestle with: how do you catch up after years of not saving? ...

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You inherit a home, and suddenly you’ve got options. In this episode, John walks through one of the most common questions people face in this situation: whether to turn it into an Airbnb or take a...

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When you leave a job, one of the biggest financial questions you face is what to do with your old 401(k). Should you roll it into an IRA? Leave it where it is? Or move it somewhere else entirely? The an...

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You’ve probably had this conversation. The family wants a pool, but you’re wondering if it makes financial sense.

But here’s the bigger question: does ever...

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When a parent dies, it’s not just the photo albums and memories that get unpacked. The house usually comes with it. And that’s where feelings and finances start bumping into each other. John...

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Living off interest sounds great, until you realize you’ve built a retirement plan that can easily collapse the moment life hits. In this episode, John uses a chicken-and-egg analogy to explain wh...

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Ever feel like you’re missing something right under your nose? On the farm, knowing all the hidden spots for eggs means a bigger haul every day, and your investments work the same way. If you know...

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John takes an everyday problem—keeping plants alive—and uses it to explain why slow, steady wealth building actually works better than chasing quick wins. He breaks down why “fake grow...

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What should you do first when your income suddenly skyrockets? Is waiting until age 70 for Social Security always worth it? In this episode, John answers a fresh round of listener questions, each one highlighting the real-life financial decisions people wrestle with every day. The truth is...

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John’s okra plants usually thrive, but this year nearly every seed failed to sprout. In this short episode, John shares how his gardening mishap illustrates one of the most important principles in investing — diversification. Whether it’s okra or your portfolio, balance ...

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Medicare can feel like alphabet soup—Part A, Part B, Part D, Advantage, Supplement—how do you make sense of it all? John talks with Ryan Nutter of Cornerstone Senior Advisors, one of the most knowledgeable Medicare specialists in the country. Together, they cut through the confusion to explain...

Sometimes the best lessons come from the most ordinary places, like the chicken coop. A simple thing like farm-fresh eggs can teach a powerful lesson about investing. Here’s the scoop: farm-fresh eggs can sit safely on your counter for weeks because of a natural protective coating called a “bloom.” But wash that coating off, and suddenly they spoil fast and need to be refrigerated.

Your investments are a lot like ...

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For decades, families have been told college is the only ticket to success. But with skyrocketing costs, shifting job markets, and the rise of AI, the economics of higher education are more complicated than ever. Career and college coach Kristin Heimstra joins John to break down how parent...

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Deciding where to live in retirement is about more than just money; it’s about lifestyle, family, and long-term comfort. In this episode, John explores the often-emotional decision of keeping the family home, downsizing, or relocating entirely. He shares real examples of weighing the...

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If you’ve ever dabbled in gardening, you know that some plants thrive together while others fight for resources. Tomatoes and potatoes? Terrible neighbors. But tomatoes and basil? That’s a match made in salad heaven. The same principle applies to your money. Certain accounts an...